3-(4-Bromo-phen-yl)-N,N-dimethyl-3-oxopropan-1-aminium chloride.

The title compound, C(11)H(15)BrNO(+)·Cl(-), was obtained as a precursor within our current program for the synthesis of new β-amino-alcohols via a Mannich-type reaction. The protonated amino N atom is hydrogen bonded to the chloride anion. With exception of one methyl group, the cation is approximately planar (r.m.s. deviation for all non H-atoms = 0.069 Å).

Related literature

For (N,N-dialkyl­amino)­propiophenones, see: Alper et al. (2002 ▶); Pupo et al. (2003 ▶); Abonia et al. (2004 ▶). For details of the synthesis, see: Brandes & Roth (1967 ▶); Vogel et al. (1978 ▶).

Experimental

Crystal data

C11H15BrNO+·Cl−

M = 292.60

Monoclinic,

a = 10.5050 (8) Å

b = 12.5694 (5) Å

c = 10.6483 (5) Å

β = 115.594 (2)°

V = 1268.06 (12) Å3

Z = 4

Cu Kα radiation

μ = 6.16 mm−1

T = 295 K

0.44 × 0.26 × 0.26 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (CORINC; Dräger & Gattow, 1971 ▶) T min = 0.61, T max = 1.00

2564 measured reflections

2564 independent reflections

2258 reflections with I > 2σ(I)

3 standard reflections every 60 min intensity decay: 5%

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.123

S = 1.12

2564 reflections

146 parameters

Only H-atom displacement parameters refined

Δρmax = 0.72 e Å−3

Δρmin = −0.65 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811041985/bt5672sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041985/bt5672Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811041985/bt5672Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H15BrNO+·Cl−	F(000) = 592
Mr = 292.60	Dx = 1.533 Mg m−3
Monoclinic, P21/c	Melting point: 495 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54178 Å
a = 10.5050 (8) Å	Cell parameters from 25 reflections
b = 12.5694 (5) Å	θ = 64–74°
c = 10.6483 (5) Å	µ = 6.16 mm−1
β = 115.594 (2)°	T = 295 K
V = 1268.06 (12) Å3	Block, brown
Z = 4	0.44 × 0.26 × 0.26 mm

Enraf–Nonius CAD-4 diffractometer	2258 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.000
graphite	θmax = 73.8°, θmin = 4.7°
θ/2ω scans	h = −11→13
Absorption correction: ψ scan (CORINC; Dräger & Gattow, 1971)	k = −15→0
Tmin = 0.61, Tmax = 1.00	l = −13→0
2564 measured reflections	3 standard reflections every 60 min
2564 independent reflections	intensity decay: 5%

Refinement on F2	Secondary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045	Only H-atom displacement parameters refined
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.0762P)2 + 0.3958P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max = 0.001
2564 reflections	Δρmax = 0.72 e Å−3
146 parameters	Δρmin = −0.65 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0047 (5)

Experimental. IR (KBr disk): 3080, 3024, 2954, 2912, 2628, 2543 (br), 2503, 2440 (br), 1684 (C=O), 1580, 1473, 1391, 1329, 1216, 1065, 1002, 963, 787 cm-1. 1H-NMR (DMSO-d6): 2.79 (s, 6H), 3.39 (t, J = 7.5 Hz, 2H), 3.64 (t, J = 7.2 Hz,2H), 7.78 ("d", J =8.4 Hz, 2H), 7.95 ("d", J = 8.4 Hz, 2H), 10.93 (bs, 1H, NH) p.p.m.; 13C-NMR (DMSO-d6): 33.2, 42.1, 51.5, 127.8, 130.0, 131.9, 134.9, 196.0 (C=O) p.p.m..

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Br1	0.31084 (4)	0.13998 (3)	0.50877 (3)	0.04655 (18)
Cl1	0.89690 (9)	−0.34411 (6)	1.32816 (9)	0.0430 (2)
O1	0.7418 (3)	0.0972 (2)	1.2059 (2)	0.0539 (6)
C1	0.4405 (3)	0.1090 (2)	0.6944 (3)	0.0374 (6)
C2	0.5264 (3)	0.0213 (3)	0.7200 (3)	0.0436 (7)
H2	0.5200	−0.0221	0.6467	0.058 (11)*
C3	0.6223 (3)	−0.0025 (3)	0.8549 (3)	0.0411 (7)
H3	0.6794	−0.0623	0.8722	0.040 (9)*
C4	0.6335 (3)	0.0629 (2)	0.9646 (3)	0.0335 (6)
C5	0.5434 (4)	0.1497 (2)	0.9364 (4)	0.0419 (7)
H5	0.5478	0.1922	1.0097	0.060 (11)*
C6	0.4478 (4)	0.1745 (3)	0.8029 (3)	0.0430 (7)
H6	0.3893	0.2336	0.7854	0.054 (11)*
C7	0.7377 (3)	0.0416 (2)	1.1111 (3)	0.0362 (6)
C8	0.8395 (3)	−0.0495 (2)	1.1373 (3)	0.0369 (6)
H8A	0.7874	−0.1160	1.1125	0.058 (8)*
H8B	0.8885	−0.0414	1.0788	0.058 (8)*
C9	0.9456 (3)	−0.0535 (2)	1.2878 (3)	0.0360 (6)
H9A	0.9986	0.0126	1.3113	0.046 (7)*
H9B	0.8957	−0.0590	1.3459	0.046 (7)*
N10	1.0466 (3)	−0.14452 (17)	1.3199 (3)	0.0358 (6)
H10	0.9959	−0.2136	1.3123	0.053 (11)*
C11	1.1447 (5)	−0.1452 (3)	1.4695 (4)	0.0578 (11)
H11A	1.2084	−0.2042	1.4889	0.082 (10)*
H11B	1.0919	−0.1518	1.5236	0.082 (10)*
H11C	1.1974	−0.0800	1.4932	0.082 (10)*
C12	1.1245 (4)	−0.1462 (3)	1.2322 (4)	0.0526 (9)
H12A	1.0585	−0.1462	1.1357	0.101 (11)*
H12B	1.1817	−0.2092	1.2524	0.101 (11)*
H12C	1.1838	−0.0845	1.2518	0.101 (11)*

	U11	U22	U33	U12	U13	U23
Br1	0.0519 (3)	0.0423 (2)	0.0400 (2)	0.00146 (13)	0.01472 (18)	0.00820 (13)
Cl1	0.0541 (5)	0.0294 (4)	0.0461 (4)	−0.0091 (3)	0.0223 (4)	−0.0025 (3)
O1	0.0644 (15)	0.0500 (14)	0.0408 (12)	0.0130 (12)	0.0166 (12)	−0.0113 (11)
C1	0.0398 (15)	0.0351 (15)	0.0376 (15)	−0.0020 (12)	0.0170 (13)	0.0041 (12)
C2	0.0492 (18)	0.0441 (18)	0.0381 (15)	0.0058 (14)	0.0193 (14)	−0.0037 (13)
C3	0.0436 (16)	0.0380 (16)	0.0418 (16)	0.0102 (13)	0.0187 (14)	−0.0025 (13)
C4	0.0364 (14)	0.0294 (14)	0.0363 (14)	0.0003 (11)	0.0170 (12)	−0.0011 (11)
C5	0.0505 (18)	0.0309 (16)	0.0444 (18)	0.0058 (12)	0.0206 (15)	−0.0055 (12)
C6	0.0519 (19)	0.0291 (15)	0.0471 (18)	0.0082 (13)	0.0206 (15)	−0.0004 (13)
C7	0.0401 (15)	0.0284 (13)	0.0406 (15)	−0.0010 (11)	0.0181 (13)	−0.0009 (12)
C8	0.0418 (15)	0.0318 (15)	0.0347 (14)	0.0019 (12)	0.0142 (12)	−0.0018 (11)
C9	0.0467 (16)	0.0270 (14)	0.0339 (14)	−0.0007 (12)	0.0170 (13)	0.0003 (11)
N10	0.0458 (14)	0.0228 (11)	0.0342 (13)	−0.0019 (9)	0.0130 (11)	0.0029 (9)
C11	0.070 (2)	0.0371 (19)	0.0411 (19)	0.0028 (16)	0.0002 (18)	0.0031 (14)
C12	0.057 (2)	0.044 (2)	0.063 (2)	0.0121 (15)	0.0319 (19)	0.0101 (16)

Br1—C1	1.894 (3)	C2—H2	0.9300
O1—C7	1.213 (4)	C3—H3	0.9300
C1—C2	1.375 (4)	C5—H5	0.9300
C1—C6	1.394 (4)	C6—H6	0.9300
C2—C3	1.385 (4)	C8—H8A	0.9700
C3—C4	1.391 (4)	C8—H8B	0.9700
C4—C5	1.390 (4)	C9—H9A	0.9700
C4—C7	1.493 (4)	C9—H9B	0.9700
C5—C6	1.376 (5)	C11—H11A	0.9600
C7—C8	1.509 (4)	C11—H11B	0.9600
C8—C9	1.507 (4)	C11—H11C	0.9600
C9—N10	1.496 (4)	C12—H12A	0.9600
N10—C11	1.477 (4)	C12—H12B	0.9600
N10—C12	1.484 (5)	C12—H12C	0.9600
N10—H10	1.0000
C2—C1—C6	120.9 (3)	C1—C6—H6	121.00
C2—C1—Br1	119.1 (2)	C5—C6—H6	121.00
C6—C1—Br1	120.0 (2)	C7—C8—H8A	109.00
C1—C2—C3	120.0 (3)	C7—C8—H8B	109.00
C2—C3—C4	120.2 (3)	C9—C8—H8A	109.00
C5—C4—C3	118.7 (3)	C9—C8—H8B	109.00
C5—C4—C7	119.3 (3)	H8A—C8—H8B	108.00
C3—C4—C7	122.0 (3)	N10—C9—H9A	109.00
C6—C5—C4	121.7 (3)	N10—C9—H9B	109.00
C5—C6—C1	118.5 (3)	C8—C9—H9A	109.00
O1—C7—C4	120.9 (3)	C8—C9—H9B	109.00
O1—C7—C8	121.1 (3)	H9A—C9—H9B	108.00
C4—C7—C8	118.0 (2)	N10—C11—H11A	109.00
C9—C8—C7	111.2 (2)	N10—C11—H11B	109.00
N10—C9—C8	113.2 (2)	N10—C11—H11C	109.00
C11—N10—C12	111.2 (3)	H11A—C11—H11B	109.00
C11—N10—C9	110.2 (2)	H11A—C11—H11C	110.00
C12—N10—C9	113.4 (2)	H11B—C11—H11C	109.00
C1—C2—H2	120.00	N10—C12—H12A	110.00
C3—C2—H2	120.00	N10—C12—H12B	109.00
C2—C3—H3	120.00	N10—C12—H12C	110.00
C4—C3—H3	120.00	H12A—C12—H12B	109.00
C4—C5—H5	119.00	H12A—C12—H12C	109.00
C6—C5—H5	119.00	H12B—C12—H12C	109.00
C6—C1—C2—C3	−0.5 (5)	C5—C4—C7—O1	2.1 (5)
Br1—C1—C2—C3	179.7 (3)	C3—C4—C7—O1	−177.0 (3)
C1—C2—C3—C4	−0.8 (5)	C5—C4—C7—C8	−176.6 (3)
C2—C3—C4—C5	2.3 (5)	C3—C4—C7—C8	4.2 (4)
C2—C3—C4—C7	−178.6 (3)	O1—C7—C8—C9	−4.1 (4)
C3—C4—C5—C6	−2.5 (5)	C4—C7—C8—C9	174.6 (2)
C7—C4—C5—C6	178.4 (3)	C7—C8—C9—N10	178.4 (2)
C4—C5—C6—C1	1.2 (5)	C8—C9—N10—C11	−178.4 (3)
C2—C1—C6—C5	0.3 (5)	C8—C9—N10—C12	56.2 (4)
Br1—C1—C6—C5	−179.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10···Cl1	1.00	1.99	2.983 (2)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N10—H10⋯Cl1	1.00	1.99	2.983 (2)	171